Windows Update is a mess: 3 things Microsoft should do to fix it

Windows Update has never been an ideal solution for maintaining PCs. There are simply too many different hardware and software configurations for it to work perfectly, or be painless. However, Microsoft has made the situation worse. The company is attempting to sweep the complexities under the rug by taking control away from users and pretending it can operate Windows 10 as a service. While that is in line with its corporate objectives, it’s frustrating many of its customers — and costing them countless hours of wasted time. Let’s look at some of the biggest problems with the current Windows Update and a way Microsoft could address each of them.

It is with a cheery tone that Forrest Gump famously explains that life is like a box of chocolates, because “you never know what you’ll get.” That is not what we want from our computer when we log in. Unfortunately, Microsoft now forces all sorts of updates — usually after a potentially data-losing reboot — on users without their explicit permission. If this was for the sake of security, that’d be one thing. But the updates includes a hodgepodge of patches, bug fixes, new features, and UI changes. Making matters worse, Microsoft has more or less stopped providing usable information about what is in each update.

Even worse than Microsoft deciding when it wants to push new features or UI changes onto your computer is when you wake up to find that a computer that worked perfectly yesterday is now not much more than a paperweight. Sometimes the situation can be fixed by Windows’ own repair utilities, sometimes with a third-party utility (at some additional expense), and sometimes not at all. Among the dozen or so Windows 10 systems I’ve used and maintained, I’ve had all three happen to me. Most recently, one older laptop turned out to have a webcam driver that would not work after a forced update. Completely removing it from the system let it work for about 5 minutes until it re-enabled itself and the system blue-screened. Short of opening up the laptop and cutting the wire to the camera, there wasn’t a good solution. We could have done a fresh install, but of course the forced update would have crashed it again.

Updates can also cause more subtle problems, including suddenly inaccessible network storage devices, and even the un-announced removal of third-party software Microsoft deems unfit to continue to exist.

Unless you are part of an Enterprise, or a user of Windows Pro who knows how to use the Policy Editor, Microsoft does not provide any way to turn off Auto Updates. You can tell them to occur outside “active hours,” but you can only have up to 12 active hours per day (and who is Microsoft to tell me when I want my computer to be usable and not rebooting?). Outside those hours, if you aren’t actively using the system, it will happily kill off your applications, and reboot as many times as it needs to in order to apply updates. That can be mildly frustrating when the updates actually work but, in a version of Groundhog Day, Windows 10 will do this over and over again — every day — if the updates fail to install.

My main work machine has gotten stuck in this cycle more than once (until I turned off Auto Update). Each time the Update / Install / Reboot to Complete Install / Failed to Install / Uninstalling / Reboot to complete Uninstall loop kept the machine occupied for about an hour. The error screen to the above right is one I plucked off it just now, while I’m writing this article. I’m lucky enough to have an office full of machines, so I could work on another one. But not everyone has that flexibility. I also found I could download and install the Group Policy editor on Windows 10 Home systems, but some sites warn against that, so do it at your own risk.

Unlike attempting to create a revolutionary new mixed-reality computing environment like Microsoft is trying to do with HoloLens, most of what Windows Update needs is simply common sense:

Imagine how refreshing it would be to have the initial Windows Update configuration screen look something like this:

It’s embarrassing to even have to ask for this. My colleague Joel Hruska has been sounding the alarm about Microsoft’s push to not bother telling people what is in its updates for a while now. Sometimes Microsoft relents a little, but for the most part, at least for end-users, update descriptions all look pretty much the same, like the one on the right. Clicking on More Info usually doesn’t actually provide any more detail, just some links about what an Update is and why, along with how like spinach, they are good for you. Microsoft used to provide a lot more of this information, so it is definitely capable of it. With a billion users, there should certainly be enough R&D money for this relatively straightforward task.

For some reason, Microsoft continues to provide arcane strings of hex digits as its excuse for error messages. In fairness, they alternate with banal test strings like “couldn’t complete the updates.” Users have a choice of doing a deep dive into log files, or Googling the hex error code and wading through incredibly long forum threads full of rants mixed with advice to “try rebooting, uninstalling anti-virus, disabling drivers, and pulling your hair out.” You can find answers that way; I learned I needed to update my encryption package at one point, and the advice to update chipset drivers is always a good reminder. But the experience is awful. Error conditions should be spelled out, and a link provided to Microsoft’s best current assessment of the problem — ideally personalized to the configuration you’re running.

Sometimes Microsoft provides a percentage complete indicator during updates. But often there is nothing on the screen for minutes — or in rare cases hours — besides a spinning ball and maybe a hopeful text message. Even when a percent complete indicator is shown, it often only relates to the specific phase of the update being run, and not to the entire process. Honest status indicators that tell you when an operation is still running or is hopelessly stuck would save users quite a bit of time and frustration.

To put this in perspective, I’m a big fan of Windows 10, and consider it a huge step forward from Windows 8 and Windows 8.1 (although many Windows 7 loyalists are not so sure). But it is not only not perfect, but in some ways, including respecting user privacy, and forced updates, it has taken steps backwards. Hopefully Microsoft will pay as much attention to these not-very-catchy fundamental issues as it is to the eye-candy it has planned for next year’s “Creators’ Update.”